Disney (DIS) chief Bob Iger has enjoyed great successes in 2019 — but the famed CEO could face greater challenges heading into 2020 as the company’s marquee properties enter critical phases.

Iger, who was just named Time Magazine’s Businessperson of the Year, dominated 2019 with a slew of big wins — which included a $71 billion acquisition of Fox’s movie assets, two Star Wars theme parks, and the release of the highest-grossing movie in cinematic history, “Avengers: Endgame.”

“Star Wars” and “The Avengers” have been the company’s bread and butter — but both narratives are beginning to reach the end of their respective journeys. “Endgame” was the grand finale for many of the film’s core characters after a decade’s worth of movies, while “The Rise of Skywalker” debuted this weekend to disappointing advance reviews — and the smallest haul of the latest “Star Wars” trilogy.

But it’s the launch of streaming service Disney+ that could really cement Iger’s legacy, which hinges on the platform’s success...or failure.

Disney+ has already seen impressive growth, with mobile app records reaching 22 million downloads since its November 12th launch, according to recent data from Apptopia.

But the cost of content is incredibly high, as Disney has already poured a reported $3 billion into the service — with Moffettnathanson projecting further losses of $4.5 billion in 2020 and $3.6 billion in 2021 as revenues catch up to expenses.

The space is also incredibly competitive — with NBC’s (CMCSA) Peacock service, along with HBO Max (T) eyeing spring 2020 launches to join Disney+, Apple TV+ (AAPL) and Netflix (NFLX) in the race for consumers.

And that’s just the beginning.

Disneyland Hong Kong has been turned into a ghost town amid the city’s ongoing protests — with weekday visitors to the theme park falling by about 90% since protests first began, according to a report in The Wall Street Journal.

But despite looming challenges, Iger will continue to double down on his risk-taking mentality.

"In ever-changing, disrupted businesses, risk-taking is essential," the executive wrote in his memoir, ‘The Ride of a Lifetime.’

"Innovation is vital, and true innovation occurs only when people have courage,” he said, adding that “fear of failure destroys creativity.”

Editor’s note: The latest “Star Wars” film is subtitled “The Rise of Skywalker.”

Alexandra Canal is a Producer at Yahoo Finance. Follow her on Twitter @alliecanal8193

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